Ch18 Amines(pdf) - KFUPM Open Courseware

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Example: Nitrosation of 1,1-DimethylpropylamineNH 2HONO+NNNitrosation of Tertiary AlkylaminesThere is no useful chemistry associated with thenitrosation of tertiary alkylamines.(80%)OHH 2 O++– N 2RRRN • •RR+NR••NO •• • (3%)(2%)Nitrosation of Tertiary Arylaminesreaction that occurs iselectrophilic aromatic substitutionNitrosation of ArylaminesN(CH 2 CH 3 ) 21. NaNO 2 , HCl,H 2 O, 8°C82. HO –N(CH 2 CH 3 ) 2N(95%)O
Nitrosation of N-AlkylarylaminesNsimilar to secondary alkylamines;NHCH 3gives N-nitrosoaminesNaNO 2 , HCl,H 2 O, 10°CNONCH 3Nitrosation of Primary Arylaminesgives aryl diazonium ionsaryl diazonium ions are much more stable thanalkyl diazonium ionsmost aryl diazonium ions are stable under theconditions of their formation (0-1010°C)(87-93%)Nitrosation of Primary ArylaminesExample:gives aryl diazonium ionsaryl diazonium ions are much more stable thanalkyl diazonium ionsmost aryl diazonium ions are stable under theconditions of their formation (0-1010°C)(CH 3 ) 2 CHNH 2NaNO 2 , H 2 SO 4H 2 O, 0-5°C0+ fastRNN+ArNNslowR + + N 2Ar + + N 2+(CH 3 ) 2 CH N NHSO – 4
Page 1 and 2: Chapter 18Amines18.1Amine Nomenclat
Page 3 and 4: Secondary and Tertiary AminesName a
Page 5 and 6: Geometry at NCompare geometry at N
Page 7 and 8: Physical Propertiesboilingpoint:CH
Page 9 and 10: Preparation of AminesTechniques fal
Page 11 and 12: Gabriel Synthesisgives primary amin
Page 13 and 14: ExampleOONHNH+ C 6 H 5 CH 2 NH 2H 2
Page 15 and 16: Synthesis of Amines via AzidesS N 2
Page 17 and 18: Synthesis of Amines via AmidesOCOHo
Page 19 and 20: Example: Secondary amines give tert
Page 21 and 22: Step 2••O••••-•• O
Page 23 and 24: Basicity Constant (K b ) and pK bK
Page 25 and 26: Basicity of Amines in Aqueous Solut
Page 27 and 28: Effect of Substituents on Basicity
Page 29 and 30: ImidazoleWhich nitrogen is protonat
Page 31 and 32: (aqueous)CH 2 CH 3+NCH 2 CH 3CH 2 C
Page 33 and 34: Nitrosyl Cation and NitrosationNitr
Page 35: Nitrosation of Primary AlkylaminesN
Page 39 and 40: The Hofmann EliminationMechanismon

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